Diisopropylethylamine → N-{3-[(2,5-dichloro-pyrimidin-4-ylamino)-methyl]-pyridin-2-yl}-N-methyl-methanesulphonamide

HRID 1255413

Reaction equation

[Cl:1][C:2]1[N:7]=[C:6](Cl)[C:5]([Cl:9])=[CH:4][N:3]=1.[NH2:10][CH2:11][C:12]1[C:13]([N:18]([CH3:23])[S:19]([CH3:22])(=[O:21])=[O:20])=[N:14][CH:15]=[CH:16][CH:17]=1.CCN(C(C)C)C(C)C>C(Cl)Cl>[Cl:1][C:2]1[N:7]=[C:6]([NH:10][CH2:11][C:12]2[C:13]([N:18]([CH3:23])[S:19]([CH3:22])(=[O:21])=[O:20])=[N:14][CH:15]=[CH:16][CH:17]=2)[C:5]([Cl:9])=[CH:4][N:3]=1

Participants

Conditions

Temperature: 0 °C

Procedure

2,4,5-trichloropyrimidine (1.0 g, 5.45 mmol) is suspended in 20 mL DCM and the reaction mixture is cooled to 0° C. Then a solution of N-(3-aminomethyl-pyridin-2-yl)-N-methyl-methanesulphonamide (1.17 g, 5.45 mmol) and DIPEA (1.95 mL, 10.9 mmol) in 10 mL DCM is added and the mixture is stirred overnight. The reaction mixture is diluted with DCM and washed 3× with 1 N NH4Cl solution. The organic phase is dried on magnesium sulphate and evaporated down in vacuo. The crude product A-2b (HPLC-MS: tRet.=2.00 min; MS (M+H)+=362) is used in successive reactions without further purification.

Workup

washwashed 3× with 1 N NH4Cl solution
customThe organic phase is dried on magnesium sulphate
customevaporated down in vacuo
customThe crude product A-2b (HPLC-MS: tRet.=2.00 min; MS (M+H)+=362) is used in successive reactions without further purification

Sources & evidence

ORD record: ord-384e284fd506437fad52d670dca5853c
Source dataset: uspto-grants-2013_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08461147B2

Linked notes

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